First off -- welcome! I think you're going to have a hard time finding something that is both easily trailerable and comfortable to stay on for a week. Obviously different people have different tolerances for stuff like motion, not being able to stand up straight, showering, etc. Maybe you should go with a smaller starter boat this year (20-23 foot). If you are handy, you can find a neglected one pretty easy, boatangel puts them on ebay all the time and they go for little to nothing, craigslist is another great option. Get your feet wet with that one, fix it up along the way, learn to sail and handle the boat, then sell it (for a profit) when you are ready to make the ICW trip and jump to something 28+ with a little more creature comfort. I'm 5'8 and have had a few boats where I had to stoop inside (O'Day 23, O'Day 26) and I just couldn't stand to be on them for more than a couple of days. Great boats, but headroom is my pet peeve I guess. Best of luck -- this is a fun process!!
